“Most people don’t believe that’s my job, but a lot of thought went into the title,” he says, enjoying the sun from the rooftop lounge of the startup’s SOMA headquarters. “Someone asked once why I wasn’t the VP of fun, but that implies there’s someone more fun than I am. And you can’t be the president of fun, because, actually, being president is never fun.”

Generally, Estrada avoids trolling the green-eyed monster by oversharing details from the merry-go-round of his life, which typically includes two or three concerts a week and time for brunch almost every day.

One exception: He couldn’t resist using a beta version of the company’s new app, Cinamatic, to work his co-workers into a froth over what they were missing out on when he was on a magazine shoot in Los Cabos, Mexico. Released today, the app lets users shoot short videos, add Hipstamatic’s signature filters and share the clips on social networks.

“To stoke the right amount of envy, they really needed to see those waves crash on that amazing beach,” he says. “Sending them the video was evil but totally effective.”

The Haus of Hipstamatic is filled with camera tchotchkes, liquor and photos.

Hipstamatic could use a little fun right about now. Launched in 2009, the company trades on selling its retro-tastic premium lenses and filters. Pro photographers developed an instant love for the company (ask Damon Winter, who won an award using it on the front page of the New York Times) and still really go for it.

The frowny face came after Instagram, a similar small, quirky frenemy startup also based in San Francisco, was bought by Facebook for a billion in 2012. Hipstamatic lost focus, trimmed down and has been trying to come back ever since. The remaining Haus denizens agree that small is beautiful, but whether they can keep the good times rolling long term without critical mass remains a question.

Inside the Fun Haus

For the last four years, Estrada, a graphic designer by trade, has wrangled acts like Surfer Blood and The Mowgli’s for live sets at the headquarters, nicknamed Haus of Hipstamatic. He also curates the company’s frequent photography shows and masterminds happy hours and brunches.

Which sounds like kind of a side thing to the real business of app making, until you visit the Haus. It’s 10:30 a.m. on a weekday and there are only three people at work this early: Mario, his assistant and CEO Lucas Allen Buick, who doesn’t even take off his motorcycle jacket before making espresso for everyone at the ground-floor bar.

Echoes of parties past are everywhere: The fridge is packed full of Pabst and IPA, and on every floor of the three-story building there’s an empty bottle of liquor standing witness. The events started as a way to showcase photographers, but when that resulted in a bunch of people standing around too scared to shoot their own candid snaps, Hipstamatic started lining up music events.

“Someone compared us to a frat house because we have these happy hour things on the roof,” he says. Likening the Hipstamatic crew to a small family, he says the endless string of parties is a bit like hosting potlucks as a way to relate to the larger community.

Estrada’s got some desk-job duties, but even those are more awesome than arduous: He’s editorial director of the company’s monthly Snap Magazine (often tailoring the editorial calendar to fit music festivals he’s attending or far-flung trips he’s taking) and reps the cool-to-be-retro outfit on social media and in its own community, Oggl.

If his job can be loosely defined as “everything we do that’s not coding the actual app,” he has sometimes doffed his Director of Fun hat and put on the more usual one of VP of special projects.

“People saw ‘fun’ on a business card and thought I was at a much lower tier,” he says. “Putting VP in front of anything makes it sound more legit. So when we work with Nike, Microsoft or Nokia, I become that.”

Hipstamatic CEO Lucas Allen Buick slings his first espresso of the day.

Socializing 101 for wallflowers

Three years ago, I met Estrada while waiting at the bar of a really bad cocktail event, the kind where everyone stands around trying to look cool but feeling ridiculous. I was definitely not having fun. We started chatting – mainly complaining about the hosts, the drinks and everyone else — and ended up having a great time.

I found out later that he’d worked one of his Director of Fun pro tips on me: Find someone who is as miserable as you are, and the two of you can roll your own fun.

“There’s a lot of awkwardness at these things, so if you’re an introvert or don’t know a lot of people, go up to someone else in the same boat,” he advises. “So much of fun is being with the people you enjoy. You’ve got to make an effort to find them.”

As you enter the Haus you are greeted by photographs, hipster furniture and more photographs.

Calibrating FOMO

Estrada, 30, admits to limiting his social media posts so he doesn’t come off as a wild-and-crazy carefree guy getting his kicks at exotic photo shoots and indie concerts while the rest of us bask in the glow of laptop screens.

“I don’t want to post consistently, because it’s not really fair,” he says. “I can’t post every concert, every meal, every photographer or musician I meet without looking like a complete jackass.”

The rooftop terrace at Hipstamatic has been home to some epic concerts and parties.

A job by any other title

In the years since Estrada donned the DoF title, the San Francisco tech scene has become crazed with creative job names (“media lumberjack,” anyone?) and also the predictable backlash, like this template that sends a protest letter to people using such whimsical job titles.

If he had to pick a new one, he says he’d go with “mixologist,” since the term describes his role as Hipstamatic’s party organizer in chief and also tips a hat to his favorite cocktail, the Old Fashioned.

“If there’s a downside to my job, it’s that I’m never off,” he says.

Estrada, who grew up in his family’s Mexican restaurant, aspires to recreate his mother’s red mole, but so far his fridge is mostly stocked with an array of hot sauces.

“In the last three years, I’d been into a grocery store maybe once,” he says. “My New Year’s resolution was to cook once a week. I’m not there yet.”